Triethylamine → HCID 178488636, compound

HRID 1884283Notes

Reaction equation

HRID 1884283 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]3[CH2:23][CH:22]([CH2:24][S:25][C:26]4[N:30]=[CH:29][NH:28][N:27]=4)[O:21][C:20]3=[O:31])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C[O:33]C1C=CC(C2C=CC(S(NC(CC3OC3)C(OC)=O)(=O)=O)=CC=2)=CC=1.CCN(CC)CC>C1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([NH:18][CH:19]([CH2:23][CH:22]([OH:33])[CH2:24][S:25][C:26]3[N:30]=[CH:29][NH:28][N:27]=3)[C:20]([OH:21])=[O:31])(=[O:16])=[O:17])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12073922Methyl 2-[(4'-methoxy[1,1'-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoateHCID 178488635HCID 178488635, compound

Product 1

HCID 178488636HCID 178488636, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

3-[(4′-Methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-2-oxo-5-[(1H-1,2,4-triazol-3-ylthio)methyl]-tetrahydrofuran: To a solution of methyl 2-[(4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl]amino-4,5-epoxypentanoate 1d (0.7 g, 1.79 mmol) in benzene (6 mL) and Et3N (0.33 mL, 2.3 mmol) at room temperature is added slowly 1H-1,2,4-mercaptotriazole (0.47 g, 4.48 mmol). The reaction mixture is stirred overnight at room temperature. Diluted with water, the mixture is extracted three times with EtOAc. The combined EtOAc layer is washed with water, brine, dried over MgSO4 and concentrated to an oil which is purified by column chromatography eluting with hexane/EtOAc (1:1) to give the desired product.

Workup

  1. extractionthe mixture is extracted three times with EtOAc
  2. washThe combined EtOAc layer is washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil which
  5. customis purified by column chromatography
  6. washeluting with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-89eacd7d70dd448fbde525e54f5632da
Source dataset
uspto-grants-2004_07
Patent number
US06762198B2

Reaction notes

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